Chiral recognition and atropisomerism in the sevoflurane dimer
Literature Information
Publication Date
2015-04-22
DOI
10.1039/C5CP01025J
Impact Factor
3.676
Authors
Nathan A. Seifert, Cristóbal Pérez, Justin L. Neill, Brooks H. Pate, Montserrat Vallejo-López, Alberto Lesarri, Emilio J. Cocinero, Fernando Castaño
View Original
Abstract
We have examined the stereoselectivity of molecular recognition between two molecules of the anesthetic sevoflurane using broadband rotational spectroscopy. The transient axial chirality of sevoflurane is revealed upon the formation of the dimer, as two different diastereoisomers made of either homo- or heterochiral species are detected in a supersonic jet expansion. The conformational assignment was confirmed by the observation of eighteen different isotopologues in natural abundance (all possible 13C's and two 18O species of the homochiral form). The two clusters are formed in practically equal proportions (1.1 : 1), probably due to their similar hydrogen bonding topologies. In both clusters the complex is stabilized by a primary C–H⋯O hydrogen bond, assisted by weak C–H⋯F interactions. This intermolecular binding regime is characterized by a mixture of electrostatic and dispersive interactions, midway between classical hydrogen bonds and van der Waals clusters.
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Source Journal
Physical Chemistry Chemical Physics
CiteScore:
5.5
Self-citation Rate:
10.3%
Articles per Year:
3036
Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.
Recommended Compounds
![4-{2-[(9H-Fluoren-9-ylmethoxy)carbonyl]hydrazino}benzoic acid structure](https://static.chemtradehub.com/structs/214/214475-53-3-bf36.webp "4-{2-[(9H-Fluoren-9-ylmethoxy)carbonyl]hydrazino}benzoic acid structure")
4-{2-[(9H-Fluoren-9-ylmethoxy)carbonyl]hydrazino}benzoic acid
CAS Number:
214475-53-3
Molecular Formula:
C22H18N2O4
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